LV13023B - 7-halo- and 7(beta),8(beta)-methano-taxols, antineoplastic use and pharmaceutical compositions containing them - Google Patents
7-halo- and 7(beta),8(beta)-methano-taxols, antineoplastic use and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- LV13023B LV13023B LVP-03-27A LV030027A LV13023B LV 13023 B LV13023 B LV 13023B LV 030027 A LV030027 A LV 030027A LV 13023 B LV13023 B LV 13023B
- Authority
- LV
- Latvia
- Prior art keywords
- deoxy
- taxol
- fluoro
- nhc
- phenyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 230000000118 anti-neoplastic effect Effects 0.000 title description 2
- 229960001592 paclitaxel Drugs 0.000 claims abstract description 208
- 150000001875 compounds Chemical class 0.000 claims abstract description 155
- -1 human ovarian cancer Chemical compound 0.000 claims abstract description 62
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 49
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
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- 125000000524 functional group Chemical group 0.000 claims description 7
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- 230000002378 acidificating effect Effects 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
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- 125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims 4
- 125000003338 L-glutaminyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C(=O)N([H])[H] 0.000 claims 4
- 125000001176 L-lysyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 claims 4
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- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 claims 4
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 3
- 125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims 2
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- 150000002367 halogens Chemical class 0.000 claims 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
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- MBBZMMPHUWSWHV-UHFFFAOYSA-N 6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNCC(O)C(O)C(O)C(O)CO MBBZMMPHUWSWHV-UHFFFAOYSA-N 0.000 claims 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims 1
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- 229910006069 SO3H Inorganic materials 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 abstract description 62
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- 208000029742 colonic neoplasm Diseases 0.000 abstract description 3
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 abstract description 3
- 208000014829 head and neck neoplasm Diseases 0.000 abstract description 3
- 201000001441 melanoma Diseases 0.000 abstract description 3
- 208000026310 Breast neoplasm Diseases 0.000 abstract description 2
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
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- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
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- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- 230000002503 metabolic effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- VLKYMHSOQDMQNF-DTWKUNHWSA-N methyl (2r,3s)-3-azido-2-hydroxy-3-phenylpropanoate Chemical compound COC(=O)[C@H](O)[C@@H](N=[N+]=[N-])C1=CC=CC=C1 VLKYMHSOQDMQNF-DTWKUNHWSA-N 0.000 description 1
- KUHYOPYTKRSGIQ-YGHPRADISA-N methyl (4s,5r)-3-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate Chemical compound C1([C@@H]2N(C(O[C@H]2C(=O)OC)C=2C(=CC(OC)=CC=2)OC)C(=O)C=2C=CC=CC=2)=CC=CC=C1 KUHYOPYTKRSGIQ-YGHPRADISA-N 0.000 description 1
- QKGSHZOMWJRBRK-ZXABPTRBSA-N methyl (4s,5r)-3-benzyl-2-(2,4-dimethoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate Chemical compound O([C@H]([C@@H]1C=2C=CC=CC=2)C(=O)OC)C(C=2C(=CC(OC)=CC=2)OC)N1CC1=CC=CC=C1 QKGSHZOMWJRBRK-ZXABPTRBSA-N 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- VGGNVBNNVSIGKG-UHFFFAOYSA-N n,n,2-trimethylaziridine-1-carboxamide Chemical compound CC1CN1C(=O)N(C)C VGGNVBNNVSIGKG-UHFFFAOYSA-N 0.000 description 1
- KRSSHLOLAUEXRL-UHFFFAOYSA-N n-(dimethylaminosulfanyl)-n-ethylethanamine Chemical compound CCN(CC)SN(C)C KRSSHLOLAUEXRL-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- LIUZBZJUDLPOPX-UHFFFAOYSA-N n-[diethylamino(difluoro)-$l^{4}-sulfanyl]-n-ethylethanamine Chemical compound CCN(CC)S(F)(F)N(CC)CC LIUZBZJUDLPOPX-UHFFFAOYSA-N 0.000 description 1
- WKQAVDBVXQOLBB-UHFFFAOYSA-N n-[dimethylamino(difluoro)-$l^{4}-sulfanyl]-n-methylmethanamine Chemical compound CN(C)S(F)(F)N(C)C WKQAVDBVXQOLBB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- KGTDRFCXGRULNK-JYOBTZKQSA-N nogalamycin Chemical compound CO[C@@H]1[C@@](OC)(C)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=C4[C@@]5(C)O[C@H]([C@H]([C@@H]([C@H]5O)N(C)C)O)OC4=C3C3=O)=C3C=C2[C@@H](C(=O)OC)[C@@](C)(O)C1 KGTDRFCXGRULNK-JYOBTZKQSA-N 0.000 description 1
- 229950009266 nogalamycin Drugs 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- DHRUXIZYVDHUCM-NMVUSRFUSA-M potassium;(4s,5r)-2-(2,4-dimethoxyphenyl)-4-phenyl-3-(2,2,2-trichloroethoxycarbonyl)-1,3-oxazolidine-5-carboxylate Chemical compound [K+].COC1=CC(OC)=CC=C1C1N(C(=O)OCC(Cl)(Cl)Cl)[C@@H](C=2C=CC=CC=2)[C@H](C([O-])=O)O1 DHRUXIZYVDHUCM-NMVUSRFUSA-M 0.000 description 1
- PQLVEGPUTCOVTA-XUKNZQTLSA-M potassium;(4s,5r)-2-(2,4-dimethoxyphenyl)-4-phenyl-3-phenylmethoxycarbonyl-1,3-oxazolidine-5-carboxylate Chemical compound [K+].COC1=CC(OC)=CC=C1C1N(C(=O)OCC=2C=CC=CC=2)[C@@H](C=2C=CC=CC=2)[C@H](C([O-])=O)O1 PQLVEGPUTCOVTA-XUKNZQTLSA-M 0.000 description 1
- MQKGQIZUCZDRIM-XUKNZQTLSA-M potassium;(4s,5r)-3-benzyl-2-(2,4-dimethoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate Chemical compound [K+].COC1=CC(OC)=CC=C1C1N(CC=2C=CC=CC=2)[C@@H](C=2C=CC=CC=2)[C@H](C([O-])=O)O1 MQKGQIZUCZDRIM-XUKNZQTLSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012257 stirred material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
- 125000002456 taxol group Chemical group 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US99057992A | 1992-12-15 | 1992-12-15 | |
US1382693A | 1993-02-02 | 1993-02-02 | |
US7633793A | 1993-06-11 | 1993-06-11 | |
US12297493A | 1993-09-17 | 1993-09-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
LV13023B true LV13023B (en) | 2003-12-20 |
Family
ID=27486333
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LVP-03-27A LV13023B (en) | 1992-12-15 | 2003-03-06 | 7-halo- and 7(beta),8(beta)-methano-taxols, antineoplastic use and pharmaceutical compositions containing them |
Country Status (26)
Country | Link |
---|---|
US (1) | US6911549B1 (zh) |
EP (1) | EP0674630B1 (zh) |
JP (1) | JP3441458B2 (zh) |
KR (1) | KR100317015B1 (zh) |
CN (2) | CN1062561C (zh) |
AT (1) | ATE226576T1 (zh) |
AU (1) | AU687027B2 (zh) |
CA (1) | CA2149021A1 (zh) |
CZ (1) | CZ291177B6 (zh) |
DE (1) | DE69332438T2 (zh) |
DK (1) | DK0674630T3 (zh) |
ES (1) | ES2187519T3 (zh) |
FI (1) | FI111633B (zh) |
HU (1) | HUT74447A (zh) |
IL (1) | IL107950A (zh) |
LV (1) | LV13023B (zh) |
MX (1) | MX9307777A (zh) |
MY (1) | MY116473A (zh) |
NO (1) | NO313801B1 (zh) |
NZ (1) | NZ259196A (zh) |
PL (1) | PL185042B1 (zh) |
PT (1) | PT674630E (zh) |
RU (1) | RU2125996C1 (zh) |
SK (1) | SK281897B6 (zh) |
TW (1) | TW389758B (zh) |
WO (1) | WO1994013655A1 (zh) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5710287A (en) | 1991-09-23 | 1998-01-20 | Florida State University | Taxanes having an amino substituted side-chain and pharmaceutical compositions containing them |
US5998656A (en) * | 1991-09-23 | 1999-12-07 | Florida State University | C10 tricyclic taxanes |
FR2697752B1 (fr) | 1992-11-10 | 1995-04-14 | Rhone Poulenc Rorer Sa | Compositions antitumorales contenant des dérivés du taxane. |
FR2698871B1 (fr) * | 1992-12-09 | 1995-02-24 | Rhone Poulenc Rorer Sa | Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent. |
US5814658A (en) * | 1992-12-09 | 1998-09-29 | Rhone-Poulenc Rorer S.A. | Taxoids, their preparation and pharmaceutical compositions containing them |
US5973160A (en) | 1992-12-23 | 1999-10-26 | Poss; Michael A. | Methods for the preparation of novel sidechain-bearing taxanes |
FR2712288B1 (fr) * | 1993-11-08 | 1996-01-05 | Rhone Poulenc Rorer Sa | Nouveaux taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent. |
GB9409131D0 (en) * | 1994-05-09 | 1994-06-29 | Erba Carlo Spa | Unsaturated taxane compounds |
FR2726272B1 (fr) * | 1994-10-26 | 1996-12-06 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
WO1996014309A1 (en) * | 1994-11-04 | 1996-05-17 | Pharmacia & Upjohn S.P.A | Taxane derivatives |
IT1275936B1 (it) * | 1995-03-17 | 1997-10-24 | Indena Spa | Derivati della 10-deacetilbaccatina iii e della 10-deacetil-14b- idrossibaccatina iii loro metodo di preparazione e formulazioni |
FR2732342B1 (fr) * | 1995-04-03 | 1997-04-30 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
FR2742751B1 (fr) * | 1995-12-22 | 1998-01-30 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
US5635531A (en) * | 1996-07-08 | 1997-06-03 | Bristol-Myers Squibb Company | 3'-aminocarbonyloxy paclitaxels |
US5773464A (en) * | 1996-09-30 | 1998-06-30 | Bristol-Myers Squibb Company | C-10 epoxy taxanes |
WO1998017656A1 (en) * | 1996-10-24 | 1998-04-30 | Institute Armand-Frappier | A family of canadensol taxanes, the semi-synthetic preparation and therapeutic use thereof |
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1993
- 1993-12-09 IL IL10795093A patent/IL107950A/en not_active IP Right Cessation
- 1993-12-09 MX MX9307777A patent/MX9307777A/es not_active IP Right Cessation
- 1993-12-13 DK DK94903483T patent/DK0674630T3/da active
- 1993-12-13 CA CA002149021A patent/CA2149021A1/en not_active Abandoned
- 1993-12-13 EP EP94903483A patent/EP0674630B1/en not_active Expired - Lifetime
- 1993-12-13 WO PCT/US1993/011827 patent/WO1994013655A1/en active IP Right Grant
- 1993-12-13 PL PL93309392A patent/PL185042B1/pl not_active IP Right Cessation
- 1993-12-13 NZ NZ259196A patent/NZ259196A/en unknown
- 1993-12-13 AT AT94903483T patent/ATE226576T1/de not_active IP Right Cessation
- 1993-12-13 SK SK788-95A patent/SK281897B6/sk unknown
- 1993-12-13 US US08/454,210 patent/US6911549B1/en not_active Expired - Fee Related
- 1993-12-13 ES ES94903483T patent/ES2187519T3/es not_active Expired - Lifetime
- 1993-12-13 DE DE69332438T patent/DE69332438T2/de not_active Expired - Fee Related
- 1993-12-13 JP JP51431294A patent/JP3441458B2/ja not_active Expired - Fee Related
- 1993-12-13 PT PT94903483T patent/PT674630E/pt unknown
- 1993-12-13 CZ CZ19951437A patent/CZ291177B6/cs not_active IP Right Cessation
- 1993-12-13 KR KR1019950702435A patent/KR100317015B1/ko not_active IP Right Cessation
- 1993-12-13 AU AU57411/94A patent/AU687027B2/en not_active Ceased
- 1993-12-13 RU RU95114377A patent/RU2125996C1/ru not_active IP Right Cessation
- 1993-12-13 HU HU9501733A patent/HUT74447A/hu unknown
- 1993-12-15 MY MYPI93002715A patent/MY116473A/en unknown
- 1993-12-15 CN CN93121129A patent/CN1062561C/zh not_active Expired - Fee Related
- 1993-12-15 TW TW082110645A patent/TW389758B/zh not_active IP Right Cessation
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1995
- 1995-06-14 NO NO19952351A patent/NO313801B1/no unknown
- 1995-06-14 FI FI952920A patent/FI111633B/fi not_active IP Right Cessation
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1999
- 1999-11-25 CN CN99124350A patent/CN1261072A/zh active Pending
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2003
- 2003-03-06 LV LVP-03-27A patent/LV13023B/en unknown
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